5 Questions You Should Never Ask Your Boss

You like to ask questions. When you meet people, you feel compelled to fire off a list of queries and learn everything you can about individuals who interest you. This can be a good thing if you’re trying to break the ice (or conduct an interrogation), but it can also be a very annoying habit depending on the situation. This is especially true when it comes to the workplace. Asking the wrong question can put you in some very awkward situations.

Work can be a minefield for social blunders. It can be all too easy to say something you later regret to co-workers, clients, and guests who stop by the office. However, the one person you want to avoid offending is your boss. If you’re a nosy Nelly, or you just have a knack for asking wildly inappropriate questions, you’ll need to rein it in a bit when it comes to work conversations. Here are five things you should never ask your boss.

1. Did you get my friend request?

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Why are you sending a friend request to your boss? Do you expect to become besties? Unless your office encourages co-workers and supervisors to be super friendly, you’re better off not sending that request. It’s unlikely your supervisor will be comfortable letting you see her private moments with her close friends and family. On the other hand, if you’ve known each other for a long time and you have become friends in real time, it might be OK. But if you’re new to the company or don’t know each other well, it’s intrusive. When it comes to social media, limit your contact to platforms catered to professionals, such as LinkedIn.

2. When are you retiring? I’d like your job someday.

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Seriously, don’t. This question is rude and shows that you’re way more concerned about your career advancement than following the basic rules of common courtesy. You might be vying for your boss’s job, but don’t let her know that. And if you’re that anxious to move your career forward, there are other ways to do that besides waiting for your boss to get old and retire. You could move on to another company, try your hand at another role within your current company, or start your own business.

3. May I leave early? I have the worst hangover.

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If you must, do all your heavy drinking and partying on the weekends. If you’re too messed up to work in the morning because you had a wild night with your buddies, that’s on you. It’s not a good enough reason to leave work early and go to sleep. And don’t ask your boss if you can nap at your desk. What you can do is use research to help ease your hangover pain, or simply call in sick and keep your drinking habits to yourself.

4. May I have more money?

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Unless you did your research and you have a list of your recent work accomplishments ready for your boss to review, don’t ask this question. You should be able to say exactly why you feel that you deserve a bump in your salary. Drowning in debt isn’t a sufficient answer. Websites such as PayScale and Glassdoor can help you figure out how much money you should be making.

5. Can we go out on a date?

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Do you really want to go there? Dating your boss might not be such a great idea. If you break up (and you most likely will), you may not have a job to come back to. In addition, depending on how you ask, your supervisor could interpret it as harassment. You may be better off pining away silently.